CN103739495A - Synthesis method of neopentyl glycol ester - Google Patents
Synthesis method of neopentyl glycol ester Download PDFInfo
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- CN103739495A CN103739495A CN201310747661.6A CN201310747661A CN103739495A CN 103739495 A CN103739495 A CN 103739495A CN 201310747661 A CN201310747661 A CN 201310747661A CN 103739495 A CN103739495 A CN 103739495A
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- acid
- dopcp
- neopentyl glycol
- synthetic method
- isocaprylic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to a synthesis method of neopentyl glycol ester, which comprises the following steps: (I) adding neopentyl glycol, benzoic acid, isocaprylic acid and a water carrying agent into a reaction kettle, and stirring and heating; (II) when the temperature in the kettle is increased to 170-180 DEG C, adding a non-acid catalyst, further heating to 200-300 DEG C, and preserving heat for an esterification reaction; (III) removing the benzoic acid, isocaprylic acid and water carrying agent to obtain a crude product of neopentyl glycol ester; and (IV) cooling the crude product of neopentyl glycol ester to 75-85 DEG C, and neutralizing, washing, rectifying, decolorizing and filter pressing to obtain the finished product. The method provided by the invention has the advantages of simple process steps, safe and stable operation, little corrosion of reaction equipment, high yield, good product quality and low production cost.
Description
Technical field
The present invention relates to the synthetic of polyatomic alcohol mixing ester class, be specifically related to a kind of synthetic method of DOPCP.
Background technology
Softening agent is the auxiliary agent kind of application quantity maximum in plastics industry, to promote plastics industry particularly the development of PVC industry play conclusive effect.Current various novel plastic has been penetrated into the every field such as industrial or agricultural, transportation, traffic, medicine, food, clothes, building, national defence.Along with the raising of countries in the world environmental consciousness, the plastics such as medicine parcel, medicine equipment, food product pack, daily necessities, toy processing have proposed higher function and safety and environmental protection requirement to primary plasticizer, and the whole world has been accelerated functional type environment-friendly plasticizer product and met the applied research of the plastics of hygienic requirements.But the primary plasticizer that at present domestic enterprise produces in many performances particularly the aspect such as wholesomeness, nontoxicity be difficult to meet the requirement of environmental protection.
Summary of the invention
The object of this invention is to provide a kind of synthetic method of DOPCP.
For solving the problems of the technologies described above, the technical solution used in the present invention comprises the steps, the first step: in reactor, add neopentyl glycol, phenylformic acid, isocaprylic acid and band aqua, then stir, heat up; Second step: when temperature in the kettle rises to 170～180 ℃, add non-acid catalyst, continue to be warming up to 200～300 ℃, esterification is carried out in insulation; The 3rd step: remove phenylformic acid, isocaprylic acid and band aqua, obtain DOPCP crude product; The 4th step: DOPCP crude product is cooled to 75～85 ℃, through neutralization, washing, rectifying, decolouring, press filtration, obtains finished product.
Proportioning raw materials in the present invention is, with molar ratio computing neopentyl glycol: (isocaprylic acid and phenylformic acid)=1: 1.6-1.9, isocaprylic acid: phenylformic acid=1:0.9-1.1.
The described massfraction that accounts for neopentyl glycol, phenylformic acid and the total material of isocaprylic acid with aqua is 1-10%, and the massfraction that catalyzer accounts for neopentyl glycol, phenylformic acid and the total material of isocaprylic acid is 0.05-1%.
Above-mentioned reaction time of esterification is 4～15 hours.
Described band aqua is toluene, dimethylbenzene or hexanaphthene.
Described non-acid catalyst is tetrabutyl titanate or titanium isopropylate.
The discoloring agent adopting in described decolorization is diatomite and gac.
New plasticizer DOPCP prepared by the inventive method is a kind of take neopentyl glycol, phenylformic acid, isocaprylic acid as the synthetic mixed ester class asepsis environment-protecting softening agent of raw material.This product does not contain phthalate, and clear tasteless is non-stimulated to environment, can be widely used in the fields such as medical packaging, toy for children, medical apparatus, food product pack, daily necessities, water inflating goods.New plasticizer DOPCP has neighbour dioctyl phthalate, the more excellent performance of diisononyl phthalate, and product meets every hygienic environment-protecting requirement of the REACH of European Union bill completely.
The invention has the beneficial effects as follows, take neopentyl glycol, phenylformic acid and isocaprylic acid as raw material, adopt non-acid catalyst, solvent is done to be with aqua to carry out esterification and is made product DOPCP, and processing step is simple, and operational safety is stable, little to conversion unit corrosion, and yield is high, good product quality, thereby production cost is low.
Embodiment
Below in conjunction with specific embodiment, technical scheme of the present invention is described, but protection scope of the present invention is not limited to this.
Embodiment 1
In the reactor of 2000ml, first to the inside, add 156g neopentyl glycol, 194.4g isocaprylic acid, 164.7g phenylformic acid, 36g toluene, then open and stir, after fully stirring, start to heat up, when rising to 180 ℃, temperature adds 1.03 titanium isopropylates, continue to be warming up to 230 ℃, be incubated 7 hours, then utilize waste heat decompression to slough phenylformic acid, isocaprylic acid and toluene (vacuum tightness >=0.08MPa), obtain DOPCP crude product, DOPCP crude product is cooled to 80 ℃, neutralization, wash with water, rectifying, collect cut, with 0.20g diatomite and 0.39kg activated carbon decolorizing, last press filtration obtains DOPCP finished product, esterification yield is 99.75%, ester content is 99.5%, yield 99%.
Embodiment 2
In the reactor of 2000ml, first to the inside, add 156g neopentyl glycol, isocaprylic acid 172.8g, phenylformic acid 146.4g, 38g dimethylbenzene, then open and stir, after fully stirring, start to heat up, when rising to 170 ℃, temperature adds 1.15g tetrabutyl titanate, continue to be warming up to 240 ℃, be incubated 8 hours, then utilize waste heat decompression to slough phenylformic acid, isocaprylic acid and dimethylbenzene (vacuum tightness >=0.08MPa), obtain DOPCP crude product, DOPCP crude product is cooled to 75 ℃, neutralization, wash with water, rectifying, collect cut, with 0.19g diatomite and 0.38g activated carbon decolorizing, press filtration obtains DOPCP finished product, esterification yield is 99.66%, ester content is 99.2%, yield 98.9%.
Embodiment 3
In the reactor of 2000ml, first to the inside, add 156g neopentyl glycol, 195.7g isocaprylic acid, 182.3g phenylformic acid, 6g toluene, then open and stir, after fully stirring, start to heat up, when rising to 180 ℃, temperature adds 0.29g titanium isopropylate, continue to be warming up to 230 ℃, be incubated 7 hours, then utilize waste heat decompression to slough phenylformic acid, isocaprylic acid and toluene (vacuum tightness >=0.08MPa), obtain DOPCP crude product, DOPCP crude product is cooled to 80 ℃, neutralization, wash with water, rectifying, collect cut, with 0.20g diatomite and 0.39kg activated carbon decolorizing, last press filtration obtains DOPCP finished product, esterification yield is 99.65%, ester content is 99.4%, yield 99.1%.
Embodiment 4
In the reactor of 2000ml, first to the inside, add 156g neopentyl glycol, isocaprylic acid 193.5g, phenylformic acid 147.5g, 24.9g dimethylbenzene, then open and stir, after fully stirring, start to heat up, when rising to 170 ℃, temperature adds 5g tetrabutyl titanate, continue to be warming up to 240 ℃, be incubated 8 hours, then utilize waste heat decompression to slough phenylformic acid, isocaprylic acid and hexanaphthene (vacuum tightness >=0.08MPa), obtain DOPCP crude product, DOPCP crude product is cooled to 75 ℃, neutralization, wash with water, rectifying, collect cut, with 0.19g diatomite and 0.38g activated carbon decolorizing, press filtration obtains DOPCP finished product, esterification yield is 99.67%, ester content is 99.3%, yield 98.9%.
Embodiment 5
In the reactor of 2000ml, first to the inside, add 156g neopentyl glycol, isocaprylic acid 172.8g, phenylformic acid 146.4g, 47.5g dimethylbenzene, then open and stir, after fully stirring, start to heat up, when rising to 170 ℃, temperature adds 2.6g tetrabutyl titanate, continue to be warming up to 240 ℃, be incubated 8 hours, then utilize waste heat decompression to slough phenylformic acid, isocaprylic acid and dimethylbenzene (vacuum tightness >=0.08MPa), obtain DOPCP crude product, DOPCP crude product is cooled to 75 ℃, neutralization, wash with water, rectifying, collect cut, with 0.19g diatomite and 0.38g activated carbon decolorizing, press filtration obtains DOPCP finished product, esterification yield is 99.56%, ester content is 99.1%, yield 98.7%.
Claims (7)
1. a synthetic method for DOPCP, is characterized in that, comprises the steps the first step: in reactor, add neopentyl glycol, phenylformic acid, isocaprylic acid and band aqua, then stir, heat up; Second step: when temperature in the kettle rises to 170～180 ℃, add non-acid catalyst, continue to be warming up to 200～300 ℃, esterification is carried out in insulation; The 3rd step: remove phenylformic acid, isocaprylic acid and band aqua, obtain DOPCP crude product; The 4th step: DOPCP crude product is cooled to 75～85 ℃, through neutralization, washing, rectifying, decolouring, press filtration, obtains finished product.
2. the synthetic method of DOPCP as claimed in claim 1, is characterized in that, with molar ratio computing, and neopentyl glycol: (isocaprylic acid and phenylformic acid)=1: 1.6-1.9, isocaprylic acid: phenylformic acid=1:0.9-1.1.
3. the synthetic method of DOPCP as claimed in claim 2, it is characterized in that, the described massfraction that accounts for neopentyl glycol, isocaprylic acid and the total material of phenylformic acid with aqua is 1-10%, and the massfraction that catalyzer accounts for neopentyl glycol, isocaprylic acid and the total material of phenylformic acid is 0.05-1%.
4. the synthetic method of DOPCP as claimed in claim 2, is characterized in that, reaction time of esterification is 4～15 hours.
5. the synthetic method of DOPCP as claimed in claim 1, is characterized in that, described band aqua is toluene, dimethylbenzene or hexanaphthene.
6. the synthetic method of DOPCP as claimed in claim 1, is characterized in that, described non-acid catalyst is tetrabutyl titanate or titanium isopropylate.
7. the synthetic method of DOPCP as claimed in claim 1, is characterized in that, the discoloring agent adopting in described decolorization is diatomite and gac.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310747661.6A CN103739495A (en) | 2013-12-31 | 2013-12-31 | Synthesis method of neopentyl glycol ester |
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| CN201310747661.6A CN103739495A (en) | 2013-12-31 | 2013-12-31 | Synthesis method of neopentyl glycol ester |
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| CN103739495A true CN103739495A (en) | 2014-04-23 |
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| CN201310747661.6A Pending CN103739495A (en) | 2013-12-31 | 2013-12-31 | Synthesis method of neopentyl glycol ester |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1426435A (en) * | 2001-02-23 | 2003-06-25 | Lg化学株式会社 | Neopentylglycol ester based plasticizer composition for polyvinyl chloride resin and method of preparation thereof |
| CN101103063A (en) * | 2005-07-15 | 2008-01-09 | Lg化学株式会社 | Hydroxypivalyl hydroxypivalate ester plasticizer composition and method of preparing the same |
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2013
- 2013-12-31 CN CN201310747661.6A patent/CN103739495A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1426435A (en) * | 2001-02-23 | 2003-06-25 | Lg化学株式会社 | Neopentylglycol ester based plasticizer composition for polyvinyl chloride resin and method of preparation thereof |
| CN101103063A (en) * | 2005-07-15 | 2008-01-09 | Lg化学株式会社 | Hydroxypivalyl hydroxypivalate ester plasticizer composition and method of preparing the same |
Non-Patent Citations (1)
| Title |
|---|
| 钮庭树: "新型增塑剂NPBIB的合成", 《精细石油化工进展》, vol. 7, no. 2, 28 February 2006 (2006-02-28), pages 30 - 33 * |
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Application publication date: 20140423 |